Application of copper(II)-mediated radical cross-dehydrogenative coupling to prepare spirocyclic oxindoles and to a formal total synthesis of Satavaptan

TY - JOUR

T1 - Application of copper(II)-mediated radical cross-dehydrogenative coupling to prepare spirocyclic oxindoles and to a formal total synthesis of Satavaptan

AU - Hurst, Timothy E.

AU - Gorman, Ryan

AU - Drouhin, Pauline

AU - Taylor, Richard J.K.

N1 - © 2018 Elsevier Ltd. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

PY - 2018/11/8

Y1 - 2018/11/8

N2 - Application of radical cross-dehydrogenative coupling (CDC) procedures to prepare a range of novel spirocyclic oxindoles and to a formal total synthesis of the vasopressin V2 receptor antagonist Satavaptan is reported. The key step involves a copper-mediated oxidative cyclisation of a simple linear anilide precursor to give the spirocyclic oxindole core. This synthetic approach was also used to prepare novel Satavaptan scaffolds and analogues.

AB - Application of radical cross-dehydrogenative coupling (CDC) procedures to prepare a range of novel spirocyclic oxindoles and to a formal total synthesis of the vasopressin V2 receptor antagonist Satavaptan is reported. The key step involves a copper-mediated oxidative cyclisation of a simple linear anilide precursor to give the spirocyclic oxindole core. This synthetic approach was also used to prepare novel Satavaptan scaffolds and analogues.

KW - Analogue synthesis

KW - Copper

KW - Cross-dehydrogenative coupling

KW - Total synthesis

KW - Vasopressin antagonists

UR - http://www.scopus.com/inward/record.url?scp=85054098569&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.09.026

DO - 10.1016/j.tet.2018.09.026

M3 - Article

AN - SCOPUS:85054098569

SN - 0040-4020

VL - 74

SP - 6485

EP - 6496

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -